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Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine

  • Jian Xiao ,
  • Yu Peng ,
  • Wei-Dong Z. Li
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  • a Engineering Research Center Biomimetic Synthesis of Natural Drugs of Sichuan Province, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031
    b Key Lab of Natural Product Chemistry and Application in Xinjiang, Yili Normal University, Yining, Xinjiang 835000
* Corresponding author. E-mail:

Received date: 2021-01-25

  Revised date: 2021-02-21

  Online published: 2021-03-12

Supported by

National Natural Science Foundation of China(21772078); Fundamental Research Funds for the Central Universities(2682019CX70); Fundamental Research Funds for the Central Universities(2682019CX71); Fundamental Research Funds for the Central Universities(2682020CX55); Program of Natural Science Foundation of Xinjiang Autonomous Region Colleges (Key Program)(XJEDU2018I018)

Abstract

Dendrobine is an important sesquiterpenoid alkaloid bearing the picrotoxane carbon skeleton isolated from the traditional Chinese medicine “Chin-Shih-Hu”. Because of structural characteristics of fused polycyclic and seven contiguous stereocenters, and exhibiting analgesic, antipyretic activities, dendrobine has attracted a great deal of attentions from both synthetic organic chemists and medicinal chemists. Over the past 50 years, there has been a number of research reports on the pharmacological activities and chemical synthesis of dendrobine. This review summarizes the biosynthetic hypothesis and synthetic advances on dendrobine.

Cite this article

Jian Xiao , Yu Peng , Wei-Dong Z. Li . Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine[J]. Chinese Journal of Organic Chemistry, 2021 , 41(7) : 2636 -2649 . DOI: 10.6023/cjoc202101041

References

[1]
Pharmacopoeia Committee of Ministry of Health, Chinese Pharmacopoeia, 2005 Edition I, Chemical Industry Press, Beijing, 2005, p.62 (in Chinese).
[1]
(中华人民共和国卫生部药典委员会, 中华人民共和国药典2005年版一部, 化学工业出版社, 北京, 2005, p. 62.)
[2]
(a) Suzuki, H.; Keimatsu, I.; Ito, K. Yakugaku Zasshi 1932, 52,1049.
[2]
(b) Suzuki, H.; Keimatsu, I.; Ito, K. J. Pharm. Soc. Jpn. 1934, 54,802.
[3]
(a) Chen,K. K.; Chen,A. L. J. Biol. Chem. 1935, 111,653.
[3]
(b) Chen,K. K.; Chen,A. L. J. Pharmacol. 1935, 55,319.
[4]
(a) Inubushi, Y.; Sasaki, Y.; Tsuda, Y.; Yasui, B.; Konita, T.; Matsumoto, J.; Katarao, E. Nakano, J. Yakugaku Zasshi 1963, 83,1184.
[4]
(b) Yamamura, S.; Hirata, Y. Tetrahedron Lett. 1964, 5,79.
[4]
(c) Onaka, T.; Kamata, S.; Maeda, T.; Kawazoe, Y.; Natsume, M.; Okamoto, T.; Uchimaru, F.; Shimizu, M. Chem. Pharm. Bull. 1964, 12,506.
[4]
(d) Huang,W. -K. Acta Chim. Sinica 1965, 31,333 (in Chinese).
[4]
( 黄文魁, 化学学报, 1965, 31,333.)
[4]
(e) Guo, L.; Frey, W.; Plietker, B. Org. Lett. 2018, 20,4328.
[5]
(a) Okamoto, T.; Natsume, M.; Onaka, T.; Uchimaru, F.; Shimizu, M. Chem. Pharm. Bull. 1966, 14,672.
[5]
(b) Morita, H.; Fujiwara, M.; Yoshida, N.; Kobayashi, J. Tetrahedron 2000, 56,5801.
[5]
(c) Meng,C. -W.; He,Y. -L.; Peng, C.; Ding,X. -J.; Xiong, L. Fitoterapia 2017, 121,206.
[6]
(a) Li, R.; Liu, T.; Liu, M.; Chen, F.; Liu, S.; Yang, J. J. Agric. Food Chem. 2017, 65,3665.
[6]
(b) X,Y. -Y.; Xu,Y. -S.; Wang, Y.; Wu, Q.; Lu,Y. -F.; Liu, J.; Shi,J. -S.. J. Pharm. Pharmacol. 2017, 69,1409.
[6]
(c) Song,T. -H.; Chen,X. -X.; Lee,C. K.-F.; Sze,S. C.-W.; Feng,Y. -B.; Yang,Z. -J.; Chen,H. -Y.; Li,S. -T.; Zhang,L. -Y.; Wei, G.; Shi, J.; Xu, K.; Ng,T. -B.; Zhu,L. -L.; Zhang,K. -Y. Phytomedicine 2019, 53,18.
[7]
(a) Cross,A. D. Rev. Chem. Soc. 1960, 14,317.
[7]
(b) Kolbe, M.; Westfelt, L. Acta Chem. Scand. 1967, 21,585.
[7]
(c) Kolbe-Haugwitz, M.; Westfelt, L. Acta Chem. Scand. 1970, 24,1623.
[7]
(d) Yamazaki, M.; Matsuo, M.; Arai, K. Chem. Pharm. Bull. 1966, 14,1058.
[7]
(e) Biollaz, M.; Arigoni, D. J. Chem. Soc.,Chem. Commun. 1969,633.
[7]
(f) Arigoni, D. Pure Appl. Chem. 1975, 41,219.
[7]
(g) Hanson,J. R.; Nyfeler, R. J. Chem. Soc.,Chem. Commun. 1975,171.
[7]
(h) Hanson,J. R.; Nyfeler, R. J. Chem. Soc.,Chem. Commun. 1975,824.
[7]
(i) Corbella, A.; Gariboldi, P.; Jommi, G. J. Chem. Soc.,Chem. Commun. 1973,729.
[7]
(j) Corbella, A.; Gariboldi, P.; Jommi, G. Sisti, M. J. Chem. Soc.,Chem. Commun. 1975,288.
[7]
(k) Cordell,A. G. Chem. Rev. 1976, 76,425.
[7]
(l) Li, Q.; Ding, G.; Li, B.; Guo,S. -X. Sci. Rep. 2017, 7,316.
[8]
(a) Yamamoto, K.; Kawasaki, I.; Kaneko, T. Tetrahedron Lett. 1970,4859.
[8]
(b) Kende,A. S.; Bentley,T. J.; Mader,R. A.; Ridge, D. J. Am. Chem. Soc. 1974, 96,4332.
[8]
(c) Hu,Q. -Y.; Zhou, G.; Corey,E. J. J. Am. Chem. Soc. 2004, 126,13708.
[9]
Yamada, K.; Suzuki, M.; Hayakawa, Y.; Aoki, K.; Nakamura, H.; Nagase, H.; Hirata, Y. J. Am. Chem. Soc. 1972, 94,8278.
[10]
(a) Mori, M.; Uesaka, N.; Shibasaki, M. J. Org. Chem. 1992, 57,3519.
[10]
(b) Mori, M.; Uesaka, N.; Shibasaki, M.; Saitoh, F. Chem. Lett. 1993,213.
[10]
(c) Mori, M.; Uesaka, N.; Shibasaki, M.; Saitoh, F.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59,5633.
[10]
(d) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1992,443.
[10]
(e) Cassayre, J.; Zard,S. Z. J. Am. Chem. Soc. 1999, 121,6072.
[11]
(a) Lee,C. H.; Westling, M.; Livinghouse, T.; Williams,A. C. J. Am. Chem. Soc. 1992, 114,4089.
[11]
(b) Lee, Y.; Rochette,E. M.; Kim, J.; Chen,D. Y.-K. Angew. Chem.,Int. Ed. 2017, 56,12250.
[11]
(c) Teichert,J. F.; Zhang, S.; Zijl, V.; Slaa,J. W.; Minnaard,A. J.; Feringa,B. L. Org. Lett. 2010, 12,4685.
[12]
Inubushi, Y.; Kikuchi, T.; Ibuka, T.; Tanaka, T.; Saji, I.; Tokane, K. J. Chem. Soc.,Chem. Commun. 1972,1252.
[13]
(a) Martin,S. F.; Li, W. J. Org. Chem. 1989, 54,268.
[13]
(b) Padwa, A.; Dimitroff, M.; Liu, B. Org. Lett. 2000, 2,3233.
[13]
(c) Padwa, A.; Brodney,M. A.; Dimitroff, M.; Liu, B. Wu,T. -H. J. Org. Chem. 2001, 66,3119.
[14]
(a) Borch,R. F.; Evans,A. J.; Wade, J. J. Am. Chem. Soc. 1975, 97,6282.
[14]
(b) Borch,R. F.; Evans,A. J.; Wade, J. J. Am. Chem. Soc. 1977, 99,1612.
[14]
(c) Roush,W. R. J. Am. Chem. Soc. 1978, 100,3599.
[15]
(a) Trost,B. M.; B.M.; Tasker,A. S.; Ruther, G.; Brandes, A. J. Am. Chem. Soc. 1991, 113,670.
[15]
(b) Sha,C. -K.; Chiu,R. -T.; Yang,C. -F.; Yao,N. -T.; Tseng,W. -H.; Liao,F. -L.; Wang,S. -L. J. Am. Chem. Soc. 1997, 119,4130.
[16]
(a) Brattesani,D. N.; Heathcock,C. H. J. Org. Chem. 1975, 40,2165.
[16]
(b) Kreis,L. M.; Carreira,E. M. Angew. Chem.,Int. Ed. 2012, 51,3436.
[16]
(c) Williams,B. M.; Trauner, D. J. Org. Chem. 2018, 83,3061.
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